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4,4'-Di-tert-butylbiphenyl, 99%, Thermo Scientific Chemicals
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Catalog number B21470.22
also known as B21470-22
Price (USD)/ Each
581.00
-
Quantity:
100 g
Price (USD)/ Each
581.00
4,4'-Di-tert-butylbiphenyl, 99%, Thermo Scientific Chemicals
Catalog numberB21470.22
Price (USD)/ Each
581.00
-
Chemical Identifiers
CAS1625-91-8
IUPAC Name4,4'-di-tert-butyl-1,1'-biphenyl
Molecular FormulaC20H26
InChI KeyCDKCEZNPAYWORX-UHFFFAOYSA-N
SMILESCC(C)(C)C1=CC=C(C=C1)C1=CC=C(C=C1)C(C)(C)C
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Specifications
Specification Sheet
Specification SheetAppearance (Color)White to pale yellow
FormCrystals or powder or crystalline powder
Assay (GC)≥98.5%
Melting Point (clear melt)124.0-131.0?C
It is used in the generation of 1,2-di(lithiomethyl)benzene. It is found to accept electrons from Li metal to give a radical anion which is highly effective in the conversion of alkyl halides to alkyllithiums. 4,4?-Di-tert-butylbiphenyl is used in production of homoallylic amine derivatives. It is also used in the preparation of lithium di-tert-butylbiphenylide, a radical anion, superior to sodium or lithium naphthalenides for metalation reactions. Along with lithium, 4,4?-Di-tert-butylbiphenyl catalyzes; reaction of chloromethyl ethyl ether and different carbonyl compounds to yield corresponding hydroxyethers and reductive opening of N-phenylazetidine.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
It is used in the generation of 1,2-di(lithiomethyl)benzene. It is found to accept electrons from Li metal to give a radical anion which is highly effective in the conversion of alkyl halides to alkyllithiums. 4,4′-Di-tert-butylbiphenyl is used in production of homoallylic amine derivatives. It is also used in the preparation of lithium di-tert-butylbiphenylide, a radical anion, superior to sodium or lithium naphthalenides for metalation reactions. Along with lithium, 4,4′-Di-tert-butylbiphenyl catalyzes; reaction of chloromethyl ethyl ether and different carbonyl compounds to yield corresponding hydroxyethers and reductive opening of N-phenylazetidine.
Solubility
Solubility in toluene; almost transparency. Soluble in dioxane: 0.1 g/mL, (clear).
Notes
Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.
It is used in the generation of 1,2-di(lithiomethyl)benzene. It is found to accept electrons from Li metal to give a radical anion which is highly effective in the conversion of alkyl halides to alkyllithiums. 4,4′-Di-tert-butylbiphenyl is used in production of homoallylic amine derivatives. It is also used in the preparation of lithium di-tert-butylbiphenylide, a radical anion, superior to sodium or lithium naphthalenides for metalation reactions. Along with lithium, 4,4′-Di-tert-butylbiphenyl catalyzes; reaction of chloromethyl ethyl ether and different carbonyl compounds to yield corresponding hydroxyethers and reductive opening of N-phenylazetidine.
Solubility
Solubility in toluene; almost transparency. Soluble in dioxane: 0.1 g/mL, (clear).
Notes
Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.
RUO – Research Use Only
General References:
- C E Neipp, et.al. The synthesis of homoallylic amines utilizing a cuprate-based 1,2-metalate rearrangement.J Org Chem.200166(2), 531-7.
- Guijarro A and Yus M. 4, 4'-Di-tert-butylbiphenyl-catalysed lithiation of chloromethyl ethyl ether: A barbier-type new and easy alternative to ethyl lithiomethyl ether.Tetrahedron Lett., 199334(21), 3487-90.
- Accepts electrons from Li metal to give a radical anion which is highly effective in the conversion of alkyl halides to alkyllithiums: Tetrahedron Lett., 1849 (1976); J. Org. Chem., 45, 1924 (1980). For use in the reductive lithiation of epoxides, see: J. Org. Chem., 55, 1528 (1990); Org. Synth. Coll., 9, 306 (1998).
- For use in the generation of 1,2-di(lithiomethyl)benzene, see Phthalan, A10217.